


Final Jeopardy

by Megg33k



Category: Supernatural
Genre: Adult Content, Angst, Angst and Humor, Extreme fluff in prologue, Gen, Humor, Jeopardy, Sexual Humor, Sexual Identity, Violence
Language: English
Status: Completed
Published: 2013-01-30
Updated: 2013-05-14
Packaged: 2017-11-27 12:01:52
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 12,135
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/661781
Author URL: https://archiveofourown.org/users/Megg33k/pseuds/Megg33k
Summary: <blockquote class="userstuff">
              <p>Supernatural Jeopardy! There's really not much more to say.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Based off of this art/post: http://tmblr.co/ZMCbQvanVXOv
> 
> I was asked several times to write a fic for it, and here it is!

Dean, Sam, and Cas walk into a bar. –rim shot–

Wha–? Oh… erm… my mistake…

Dean, Sam, and Cas (actually) walk into a bar.

***

“Got anything, Sammy?” Dean asked, sprawled on the bed watching cartoons and eating a burger straight from the Styrofoam container.

“Yeah, maybe. Get this…” Sam peeked out from behind his laptop. “Five people, seemingly unconnected, all left the same bar last night and woke up dead.”

“Dead people don’t wake up, Sam. You, of all people, should know–”

“Figure of speech, Cas. Okay… five people. That’s a lot, but what’s this got to do with us?”

“Well, they were all killed by falling studio lights–”

“And…”

“–inside their homes.”

“Oh.”

“We should check out the company that installed those lights–”

“They didn’t have studio lights installed in their houses, Cas.” Sam pressed his fingers to his forehead and temple, as if he was warding off an impending headache, and sighed. “The only clue found at each scene was a hole in the ceiling directly above the body… which was especially strange since one of them died on the 2nd floor of a 10 story apartment building.”

“Does the hole go… ya know… all the way up?”

“No, apparently. And there are no holes in the floors or ceilings of the apartments above it, but… well…”

“Well?”

“Well... when you look through the hole…” Sam paused and squinted at the screen. “Just come look; there’s a picture.”

Dean made his way around the table and leaned over Sam’s shoulder to get a better view. “Is… is that… _the sky_?”

“Yeah.”

“Sounds like our kind of thing.” Cas was suddenly at Dean’s side and smiling proudly. “Where are headed?”

“The Yankee Clipper in Ankeny, Iowa.”

“What the hell is an _Ankeny_?”

“Uhm… I don’t know, but this website says they have Taco Tuesday. And today’s–”

“Monday!” Dean’s eyes lit up. “We roll at 8!”

***

So, where was I? Oh, right…

Dean, Sam, and Cas (actually) walk into a bar. Dean headed straight for the line of barstools, mostly empty considering it was 3PM on a Tuesday afternoon, and took the one nearest the door. By the time Sam and Cas caught up to him, the bartender had already slid three bottles of beer in their direction, one for each of them.

“From him.” The bartender nodded toward an empty corner. “Hmph. He was just there a minute ago… whatever.”

Dean eyed his bottle warily, not quite certain why he felt so compelled to drink it and even less sure of why Sam and Cas were already drinking theirs. He was lifting it to his mouth before he had even decided to take a drink, and no sooner had it touched his lips, the bar around him fell away.

He stood at a podium, Sam to his right and Cas to his left. Sam’s name was scrawled on the screen at the front of him podium, and Dean assumed his was as well. Cas’ read, _I DON’T UNDERSTAND WHAT I NEED TO WRITE MY NAME FOR._ Of course he didn’t. It may have even been funny under other, less I-may-be-high-as-balls circumstances.

In front of them and off to the right was a wall of television screens, categories at the top and dollar amounts running from $100 to $500 in vertical columns. And, if that wasn’t unsettling enough, they were punctuated with the presence of one very smug-looking trickst– Er… Gabriel… complete with a fake moustache that wouldn’t even fool Roy LeGrange.

Gabriel… back from the grave? What else was new? No one seemed to stay dead anymore. The idea of Gabriel hosting Jeopardy, however… _that_ was terrifying. Especially with categories like Character Flaws, Betrayal, People Who Are Dead Because of You, Worst Nightmares, Sexual Humiliation, and Words You Can Never Take Back.

Until that moment, Dean’s memories of Jeopardy were all sort of happy… or as close a facsimile as the Winchesters’ lives allowed. Sammy had always been a bit more ‘book smart’ than he was, had a tendency to be a few steps ahead in the brainier subjects. So, growing up, Jeopardy served to provide some of the mental stimulation that Dean often failed to offer.  And he suddenly hoped his baby brother would be as good a player in person as he always had been from the sofa as a kid.


	2. Chapter 2

“This is Jeopardy!”  A disembodied voice boomed across the stage, televisions dimming and lighting up in succession. “Let’s welcome tonight’s contestants.  A law school dropout from Lawrence Kansas, Sam Winchester. Daddy’s little foot-soldier also from Lawrence Kansas, Dean Winchester. And once-fallen and never quite right Angel of the Lord, Castiel.”

Then the spotlight fell to Gabriel. “Hello and welcome to our program. Sam, Dean, I’m sure even a couple of knuckle-draggers like yourselves must have seen this show a few times. And Castiel… well… you never really know what’s going on anyway, do you? So, let’s get this party started, shall we? You’re up, Sam!”

“What do I do?” Sam whispered out of the corner of his mouth, shooting Dean a sideways glance.

“Ah, ah, ah.” Gabriel tutted his disapproval. “No conferring with the other players.”

Dean set his jaw and hissed through gritted teeth. “Just pick a category. Play the damn game.”

“Uh… I guess I’ll take Character Flaws for $100, Al– Gabri– Ya know what? Whatever.”

“That’s the spirit!” Gabriel beamed disingenuously. “Character Flaws for $100. Fingers on buzzers.” The television in the proper grid space flickered, the dollar amount changing to the answer. “This person doesn’t understand your references, including this one.”

_–buzz–_

“Sam.” Gabriel pointed.

“Cas.”

“Yes?”

“No, Cas.” Sam pinched the bridge of his nose. “That’s the answer.”

“Ooh… so close! Anyone else want to try?”

_–buzz–_

“Go ahead, Dean.”

“ _Who is_ Castiel?” Dean glared at Sam.

“I’m Cas. What are you doing? Why don’t you remember me, Dean?”

“Correct!”

“I do remember, Cas. You’re the answer to the question.”

“But you asked who I was. I don’t understand.”

“Aww...” Gabriel puffed out his lip in a faux-pout. “Did I forget to review the rules?”

“Answers have to be given in the form of a question. Get it?”

 “I-I’m not sure.”

“Perfect.” Dean cracked his neck. “This is gonna be a long damn game.”

“Well, we’re already off to one hell of a start, wouldn’t you say? Pick your poison, Dean.”

“Fine. Character Flaws for $200.”

“Character Flaws for $200. This person is still struggling to come to terms with his bisexuality.”

_–buzz–_

“Ca—Castiel?”

“Who is Dean Winchester?”

Both Winchesters’ heads whipped toward Cas simultaneously, but only Dean spoke. “Cas! What the hell?”

“I’m sorry, Dean,” Cas replied in a poor attempt at a whisper. “But you seem to forget I can hear your thoughts.”

“Wha—No… I…”

“That’s… correct. I’ve gotta admit, Castiel, I didn’t expect you to get the hang of this… like… _ever_. I guess there’s a first time for everything, though. That means you get to choose the next category.”

“I’ll take Sexual Humiliation for $100.”

Dean and Sam squirmed a bit at Cas’ decision, Dean clenching and unclenching his fist a few times for posterity.

“Excellent choice! Dean wore _this_ article of clothing at a past girlfriend’s request and _liked it_.”

All eyes were on Dean when he worked up the nerve to look around. “Oh, come on! You’ve gotta be kidding me.” With a wince, he pressed his buzzer.

_–buzz–_

“Yessssssss?” Gabriel asked in a giddy, nearly sing-song tone.

 “What are pink, satin panties?” Dean’s voice was barely a whisper.

“What was that?” Gabriel choked back a smirk. “I couldn’t quite hear you.”

Sometimes a whisper can turn into a snarl, and this was just such an occasion. “I said, ‘What are pink, satin panties?’”

“Dean, Dean, Dean. Never pictured pink as your color. I believe… wait…” Gabriel pressed a finger to his ear. “Yes, it seems we have a photo. Let’s take a look, shall we?”

Sam snickered as the photo flashed onto the monitor, though Cas seemed completely un-phased.

“Go ahead, Sammy. Laugh it up!”

“Sorry… I just… there’s ruffles on the b–”

“Shut up!”

“Shutting up, shutting up.” Sam cleared his throat in a failed attempt to compose himself. “Sorry.”

“Oh, man. Do I have good ideas, or what?” Gabriel continued giggling as he spoke. “Okay, Dean. What’ll it be?”

“Let’s try Character Flaws for $500.”

“The other half of Sam’s most successful relationship to date, despite being a bit clingy.”

Confused expressions befell Sam and Dean, though Cas seemed lost in thought.

_–buzz–_

“Dean.”

“Who is… Jessica?”

Sam’s mouth hung agape. “Dean! How could you say–”

“Nice try, but wrong.”

_–buzz–_

“Sam.”

“Who is Amelia?”

“You call that successful?” Gabriel snorted derisively. “Wow. No. It’s up to you now, Castiel.”

_–buzz–_

“Are you referring to Lucifer?”

“Well, I suppose that _is_ in the form of a question. Two out of two for Castiel, and the choice is yours once again.”

“Seriously? Lucifer? That’s not–”

“It’s not what, Sam? Fair? True?”

“Shut it, ya junkless sissy!” Dean snapped.

“Aww… Would you look at that? Big brother coming to little brother’s defense. Isn’t that touching?”

“It’s… fine, Dean. Just pick the next category and get it over with, Cas.”

“Alright. Sexual Humiliation for $200.”

“Goddammit, Cas!”

“Tsk tsk tsk, Dean… There’s no need to bring Dad into this.” Gabriel glanced to the proper screen with a smirk. “Ah, memories. This is the location from which Dean retrieved Holy Oil once used against yours truly. And you should be as specific as possible.”

_–buzz–_

“Sam.”

“What is the trunk of the Impala?”

Gabriel narrowed his eyes and pursed his lips. “Did you really think that was going to work? The category _is_ sexual humiliation. I suggest you all keep that in mind before trying again.”

_–buzz–_

“Dean.”

Dean huffed out a long-suffering sigh. “What is Sammy’s ass?”

“As eloquent as ever, I see. But nonetheless correct. Nice work. Now, we have to take a short commercial break. But, first, let’s check out the scores. We have Castiel in a commanding lead with $700, followed by Dean with -$100, and Sam bringing up the rear with… ouch… -$700. At least you dropped out of school before you flunked out.” Gabriel paused only until Sam opened his mouth to speak and promptly continued. “And now a word from one of our sponsors.”

In an instant, Dean and Cas found themselves seated on the edge of motel bed. With green and orange floral drapes hanging haphazardly from a cracked window, the room itself had seen better days. And the lava lamp on the bedside table made it clear that that no one had bothered updating (or cleaning, from the looks of it) the place since Woodstock.

Dean stared at the cue cards in front of him, boldly displaying dialogue he was loathe to speak but knowing full well the game had to be played. “So, did it hurt?”

“Did what hurt?”

“When you fell from Heaven.” Dean smiled against his will.

“Yes. Quite a lot. Why would you bring that up right now, Dean? Now hardly seems like the time.” Cas replied, obviously unaware that he was meant to say the lines written on the poster board signs.

“Cas!” Dean hissed out of the corner of his mouth, his fake smile never falling away. “You’re supposed to read your lines.” He jerked his head roughly toward the cue cards.

“What are you—Oh… ohhhh. I understand now. I can do this. Just give me the line again.”

“When you fell from Heaven.”

“Oh, you!” Cas replied in the sickeningly sweet tone the card indicated he should use. “If I said you had a beautiful body, would you hold it against me?”

“You bet I would.” Dean blinked slowly and steeled himself before holding up a box of Trojan condoms. “And, when I do, I’ll do it safely.”

Cas pointed at the box. “Look! They’re ribbed… for _my_ pleasure.”

“And mine!” Dean winked, and he and Cas fell into one another’s arms just as the lights went down.


	3. Chapter 3

As quickly as Dean and Cas had been transported to the set of their little commercial endeavor, they were back behind their podiums.

“And welcome back! Bravo, boys! Lovely performance, I must say. Shall we continue? I believe Dean gets to choose the next category.”

“Let’s try Character Flaws for $300.”

“ _His_ greatest weakness seems to be the inability to find a good barber.”

_–buzz–_

A grin spread across Dean’s face, his fondness for that particular category suddenly increasing ten-fold. “Who… ah…” He paused to snicker. “Who is Sam?”

“Correctamundo!”

“What? My hair? That’s the best you could come up with?”

“No speaking out of turn, Samson!” Gabriel chided, eliciting the squaring of Sam’s shoulders but the silencing of his tongue. “Your pick again, Dean.”

“Let’s just finish off this bitch, shall we? Character Flaws for $400.”

“Character Flaws for $400 it is. _This person_ suffers from extreme trust issues.”

_–buzz–_

“Sam.”

“Who is Dean Winchester?”

“Wrong.”

“But he does,” Cas interjected. “I’m sure of it.”

Gabriel did little more than point at Cas before a pristine strip of duct tape appeared over his mouth. “Not without buzzing in!”

Dean's eyes darted between his brother and his angel, unable to decide who most deserved the scowl that had settled on his face. His face was still warm with anger when he depressed his buzzer.

_–buzz–_

“Who is Sam?”

“Nice try, Dean. Really. But no again.”

_–buzz–_

Cas gently peeled the tape from his lips. “Who is… me?”

“Wrong again! Though I respect your self-awareness, Castiel. No, boys… the answer I was looking for was EVERYONE YOU KNOW!”

“What?” Dean began. “How’s that–”

“Fair? I don’t suppose it is. It was a bit of a trick question. It’s not like you should have come to expect that from me…” Gabriel stopped and looked himself up and down. “Oh, right. Yes, you should. Let’s move on. Still your choice, Dean.”

Dean grunted with discontent. There wasn’t a single category on the board he _wanted_ to face, so he went in order. “Betrayal for $100.”

“From trust issues to betrayal in one easy step? Sounds like the story of your lives. Maybe you should write it. Just imagine the movie deal.”

“Hardy har har. Just read the damn question.”

Gabriel raised his hands in a sarcastic simulation of surrender. “Betrayal for $100. _She_ was the opportunist who made one deal she couldn’t ditch.”

_–buzz–_

"Sam."

“Who is... Bela?”

“Do my ears deceive me? Or has Sam actually gotten something right? Quick! Someone note the date and time, alert the media.”

Sam simply crossed his arms and scanned the remaining categories. “Betrayal for $200.”

No sooner had the words left his mouth, something akin to the sound of lasers in a bad sci-fi movie sounded. “Oh! Daily Double! Well… since you currently have–” Gabriel peeked at the dollar amount on Sam’s podium. “– _negative_ $1100, you can wager up to the round maximum.” His voice dropped to a faux-whisper. “That’s $500, in case you’re as bad at math as you seem to be at everything else.”

“$500 it is.” Sam glowered.

“Excellent! For $500. _She_  is the demon who made Sa– well… _you_ an offer you couldn’t refuse, even at the cost of betraying your brother, and then betrayed you in return.”

With only an apologetic half-glance toward Dean, Sam answered without hesitation. “Who is Ruby?”

“Two in a row. Color me impressed. What’s next?”

“Same. $300.”

“ _He_ came back from Lucifer’s cage without a soul and kept it to himself for a year.”

_–buzz–_

“Who is–” Sam sighed. “–me? Er… who… am I?”

“Isn’t that the question we all ask ourselves, Sam? But now’s no time for pondering life’s great myster– Oh… oh! That’s your answer? Well, yes. Correct. I’m so sorry, I just can’t get used to you giving the right answers. Still losing, but by slightly less, you now have a total of -$300. Dean’s in second place with -$200. And Castiel is still leading the way with _positive_ $300. I must say, I expected worse. More of the game when we return, but first…”

Sam was gone from Dean’s side and out of sight until a spotlight flickered to life. He was sitting in a salon chair, legs crossed and hands poised on his knee. The chair, first seen from behind, spun toward the audience.

“Want chair-worthy hair every day?” Sam tossed his hair comically with both hands. “The pH activated moisturizers in TRESemmé’s shampoos target the site of damage and prepare hair for conditioning. This helps conditioners work better, because they know exactly where hair needs moisturization.” He reached for two bottles on the table beside him and held them up with a camera-ready smile. “For visibly smoother, salon vibrant, chair-worthy hair without the salon price – TRESemmé. Professional. Affordable.”


	4. Chapter 4

**Notes for the Chapter:**

> OMG! I'm so sorry this took so damn long. Forgive me? I'm hoping the next chapter will be up really, really soon. I need to just get this done. It only gets heavier and less funny as it goes though. Be prepared for a bumpy ride.

“And we’re back! Can I get a round of applause for Sam here?” Gabriel stared out at the silent audience. “No? Okay, then. Where to next?”

Sam chose with a grimace. “Betrayal for $400.”

“He slaughtered his brethren and decimated his home.”

_–buzz–_

“Castiel.”

“Th-that was… me.”

“Th-that was the sound of you falling into the negative,” Gabriel mocked. “Someone want to show Castiel where he went wrong?”

_–buzz–_

Dean dropped his gaze toward his depressed buzzer and placed a hand on Cas’ forearm. “Who… uh… who is Castiel?” He cleared his throat just for the sake of doing it. The words had hurt more on their way out than seemed necessary, the pain on Cas’ face like a dagger to his heart. “Sorry, man,” he whispered.

“Not even half as sorry as I am,” Cas replied without so much as looking up.

“Aww… It’s almost like watching a Lifetime movie. That’s also the correct answer. Your choice, Dean.”

“Betrayal for $500.”

“Castiel helped Zachariah imprison Dean in this significant place as they waited for the Apocalypse.”

_–buzz–_

“Castiel… again.”

“Wha—where? Where is the green room? And I’m still sorry about that, Dean.”

“I know. It’s fine,” Dean mouthed, his reply little more than word shaped breath.

“Someone’s learning! That's correct. Back in the positive and your choice.”

“Words You Can Never Take Back for $100.”

“I’ll give you the quote, and you tell me who said it. Here we go. ‘Sometimes you two are the whiniest, most self-absorbed sons of bitches I’ve ever met.’”

_–buzz–_

Dean smiled a sad smile. “Who…” He paused, coughed out a chuckle. “Who is Bobby Singer? But… uh… you got it wrong.”

“Wrong? Care to enlighten me?”

“My pleasure.” Dean smirked. “It’s ‘whiniest, most self-absorbed sons of bitches _I_ ever met.’ You said ‘ _I’ve_ ,’ but it’s just ‘ _I_.’”

“And how would you possibly remember a thing like that?”

“Yeah, Dean.” Sam nudged him. “I don’t remem–”

“No? Well, I do. I’ve replayed those words in my head more times than you can count, let Bobby keep me in check even from beyond the grave. I can hear ‘em, Sammy… every night… right here.” He ground his fingertip hard against his temple. “And never once has he ever said ‘ _I’ve_.’”

“Dean, I… never realiz–”

“Nah.” It came out as a growl, his face hardening. “Don’t even worry about it. Same category. $500. Bring it.”

“As you wish.” Gabriel held his hands up in feigned surrender. “I was dead from the moment we said hello.”

Dean’s thumb twitched over the button, but they weren’t words he recognized. And a quick glance at Cas confirmed he was as clueless as ever. But Sam.

Sam’s face had gone pale with a greenish hue. His jaw was set, his teeth clenched. His knuckles were white where they wrapped around the buzzer, and it was clear the question was meant for him.

_–buzz–_

“Sam.”

Sam screwed his eyes shut tight and let out a deep breath Dean hadn’t seen him take. “J—Who is Jess—Jessica Moore?”

Sam’s expression was so rigid, his features so unmoving, Dean thought he might have a healthy future as a ventriloquist if he ever got out of the family business. But he didn’t like that train of thought very much and moved on quickly. His attention again focused on Gabriel, who must have been telling Sam he was correct. There was really no doubt, even if he hadn’t been listening to hear it himself.

Sam was already making his next choice. “Same. $200.”

“Fan favorite, it seems. You asked for it. This one is more of a fill in the blank. Ready? ‘ _[He]_ has been more of a brother to [Dean] this past year than Sam’s ever been. That’s right. _Cas_ let [Dean] down. _Sam_ let [Dean] down. _[He]_ is the only person who hasn’t let [Dean] down.’”

Dean could feel Sam glaring, but he refused to meet his gaze. He also refused to press the buzzer and say—

_–buzz–_

“Who is Benny?” Sam snarled it for him, through gritted teeth.

“Did you really say that, Dean?” Cas asked, and he had the audacity to look hurt.

“You sent me home alone,” Dean whispered as angrily as a whisper can sound. “You left me, and Sam didn’t look for me, and… and… yes. Okay? I said it.”

“You must have felt so alone. That was never my intention. I didn’t stay becaus–”

“If you two are done,” Gabriel chimed in, “it’s time for another commercial break. But first, the scores! Sam and Castiel are tied at $400, and Dean is right behind them…" He made a poor attempt at obscuring the view of his lips and spoke from the side of his mouth. "What else is new, am I right?” And waited for canned laughter that never came. He scowled before straightening himself up and continuing. “Any- _gay_ … er… any- _way_ , Dean is right behind them with $300. It’s a tight one.” He snickered before answering himself, “That’s what he said.” A rimshot sounded somewhere in the distance.

Dean rolled his eyes. “Just get on with it, will ya?”

“Ah ha ha. That _is_ what he said.” Cas laughed to himself, shaking his head. “I understand now. That’s very funny. It would be hilarious is Enochian.”

Dean closed his eyes to cringe and opened them to the wrong side of a closed door. Before he could knock, it opened to an equally bewildered Sam.

“I must have the wrong house.” Dean spoke the words from the cue card.

Sam grinned, thumbing at himself with a big, goofy grin. “Brother.” They embraced, though it was probably more awkward than intended. “Oh, I missed you so much.”

“I waited up all night for you, you know?” Sam continued as they instinctively walked toward a kitchen that neither of them had ever been in before.

“It’s a long way from Purgatory.” Dean stopped to sniff a coffee pot, practically against his will. “Ah! Real coffee.”

They froze as a video of their parents’ bedroom was displayed. The bed was empty and obviously hadn’t been slept in for quite some time. The camera panned to a small nightstand with a frame on it. Inside the frame were the newspaper clippings of John's and Mary's obituary.

Dean shuddered, his voice seemingly forced from his body. “I brought you something from far away.” He held out a small, wrapped box.

“Really?” Sam smiled the most insincere smile Dean had ever seen and took the gift. “Aw.” He pulled the bow off and stuck it to Dean’s shoulder.

“Heh.” Dean chuckled. “What’re you doin’?”

“You’re my present this year.” Sam blushed.

The card suggested an ‘ _incredibly gay, incestuous look_.’ They complied, whether they wanted to or not.

A voiceover sang out, “The best part of waking up is Folgers in your cup.”

**Notes for the Chapter:**

> If you don't know what I'm talking about with the commercial, you can watch the original here: http://youtu.be/zZnqBL6iYjA
> 
> It was sort of a big thing for a while. There's an amusing DailyDot article about it, too. You can read it here: http://www.dailydot.com/society/folgers-incest-holiday-commercial-family/
> 
> I just couldn't help myself... especially with how often Sam and Dean used to get accused of being a couple. XD
> 
> Hope you enjoyed. Feel free to tell me all about it in the comments. ♥


	5. Chapter 5

**Notes for the Chapter:**

> Look at me! Two chapters in two days! Holy fuck! *checks my own temperature*

Gabriel clapped, slow and obnoxious. “Oh, now that was beautiful. Brotherly love at its very best.”

Back in front of their podiums, it was once again Sam’s turn to choose. He cleared his throat, blatantly ignoring their not-so-gracious host. “Sexual humiliation for $500.”

“If you say so.” Gabriel smirked as the TV flipped from monetary amount to answer. “The reason the Winchester brothers are so often mistaken for a gay couple.”

Sam and Dean were busy whispering back and forth to one another when suddenly—

_–buzz–_

“Castiel.”

The angel fidgeted, the gears in his brain obviously working overtime. Despite his expression of uncertainty, he spoke with clarity. “What are Dean’s overt attempts to live up to masculine stereotypes due to his inability to accept his bisexuality, and Sam’s sensitive, caring nature often attributed to femininity? While Dean tries so hard to be the picture of masculinity, he often becomes a caricature of it instead, which is sometimes looked upon as overcompensation. And Sam is often more emotional than the typical male, breaking commonly accepted gender roles. Also, Sam’s hair. I mean… what is… also… Sam’s hair?”

The brothers stared, gaping at the Cas, who had just psychoanalyzed them in ways to which they weren’t quite accustomed. In fact, Dean was certain he wasn’t in even in the same zip code with 'being accustomed’ to that level of scrutiny. Not even in the same damn state. “What the hell, Cas?”

“I’m sorry, Dean. I… I’ve been studying you for a very long time. I’m sure that was difficult for you to hear, but I would very much like to win this game.” Cas turned his attention back to Gabriel. “I was correct, wasn’t I?”

Gabriel studied the card in his hand before looking up again, his eyes narrowed. “We actually had, ‘Isn’t it obvious?’ But I’m gonna give it to you anyway." He motioned toward the remaining categories. "Your choice.”

Cas beamed. “I’ll take Sexual Humiliation for $300.”

“For $300. _He_ got an erection upon seeing Castiel cleaned up after his return from Purgatory.”

_–buzz–_

“Castiel.”

“Who is Dean?” His smile grew wider, clearly proud of himself.

“Cas!”

“This is what I was saying earlier about your repressed bisexuality, Dean. But it’s okay. Sam already knows, and I’m indifferent to sexual orientation. In fact, I find it rather… flattering. You know, I wouldn’t be opposed to allowing you to expl–”

“Whoa. Is this Jeopardy? Or Love Connection? Break it up, you two.” Gabriel glowered at the both of them, discouraging further discussion.

But did Cas just offer to—

“Choose again,” Gabriel continued before Dean could finish his thought.

“We’ll discuss it later,” Cas whispered. “I'd like to finish the category.”

“Sexual Humiliation for $400. _This_ is the relationship most heralded by the fans of the Supernatural book series.”

_–buzz–_

Sam let escape a long-suffering sigh. “What is Sam slash Dean.”

“Correct! And why do you think that is? Oh, wait… Castiel already told us.” Gabriel grinned at the blushing brothers. “Your choice. And a friendly reminder that People Who Are Dead Because of You and Worst Nightmares have yet to be chosen. Surely a simple oversight.”

“Yeah, oversight.” Sam scoffed. “Words You Can Never Take Back for $400.”

“Fine. Be that way.” Gabriel rolled his eyes as he waited for the screen to change and finally read, “I just don’t look at family the same way you do.”

_–buzz–_

“Dean.”

“Who is... uh… Sammy?”

“Bonus points if you know who he said it _to_ ,” Gabriel taunted.

“Yeah. ‘Course I know who he said it to. He said it to me. What do I get?”

“Nothing. I lied. Just wanted to make you say it.” Gabriel flashed a wicked smile and shrugged. “You boys are too easy.” Then his expression fell to a playful pout. “But don’t be mad. I’ll still let you pick the next question.”

“Fine. Finish the category,” Dean replied with a grimace.

“Spoil sport. You can’t avoid those others forever, you know.”

“Nope. But I can for now. So, shut your pie hole and finish the damn category, will ya?”

“Touchy!” Gabriel bobbed his head sassily and spoke in deadpan. “For $300. ‘You’re not my family, Dean. I have no family.’”

_–buzz–_

“Dean.”

“Who is Cas?”

Cas opened his mouth to speak, but Dean effectively raised a hand to stop him.

“Correct. And that brings us to the end of another round. First, scores. Cas is in the lead with $1200, followed by Dean with $1000, and Sam bringing up the rear with $800. I must say, I thought you’d all be doing much worse by now. Still plenty of time though.” He winked. “And now a word from our sponsors.”

In the blink of an eye, Cas was no longer at Dean’s side. Instead, he was across the stage, wearing nothing but gym shorts, tube socks, and sneakers. He looked as confused as Dean felt, his entire being fighting against the heat swirling in the pit of his stomach at the sight of the scantily clad angel of the lord. _I am not a repressed bisexual. That’s just—_

“This is not a workout,” Cas read, as he shook a dumbbell-like object in his hands. “This is a revolution. This is… Shake Weight… for men. And it’s going to kick your assbutt… in just six minutes… guaranteed.” He shook the weight toward his face, in an action that couldn’t be called anything but suggestive. “Ordinary weights isolate one muscle in one direction, but Shake Weight harnesses the power of dynamic inertia to totally redefine strength training.”

Cas lowered the weight near his groin and pumped it repeatedly, in a way that was a far cry from anything akin to family friendly. His breaths were sucked in sharply through his teeth, his face strained. And, when he exhaled, he did so from between parted lips, relief washing over him each and every time. Calling it sexual wouldn’t even have begun to accurately describe what Dean was seeing. “As you shake, the weights at each end fire and recoil rapidly. This piston-like motion sends a shockwave of energy that–”

 _Blah blah blah._ It didn’t matter. Dean’s blood flow has long since abandoned the parts of his body he used to listen to and process speech. In fact, he could focus on little other than his dick being jealous of a piece of exercise equipment and how ‘repressed’ had suddenly vanished from every dictionary on the planet. Because _God. Damn_.

“And now, this technological breakthrough in strength training can be yours for just $29.95,” Cas continued. “Shake Weight is science fact, not fiction.”

And Dean didn’t care. All he cared about was replacing that weight with his cock. And, embarrassing as it may have been, he was pretty sure he wouldn’t need anywhere near six minutes.

“Get ripped… defined… stronger… faster… guaranteed. Call now.”

Cas’ words morphed in Dean’s head. They became, “Harder, deeper, faster, fuck me. I’m cumming.”

Holy hell, he _really_ didn’t fucking care. Dean was hard and sweating and could barely remember how to breathe, but he didn’t mind it, not one bit. At least he was feeling _something_. Because, when you’re Dean Winchester, feeling something for another living creature is about as much as you should ever hope for.

**Notes for the Chapter:**

> You've seen the commercial. I couldn't help myself. I just... I have no excuses. And I'm not sorry... not at all.
> 
> This is actually the last of the not-stupidly-painful chapters. I mean, there's a reason Sam, Dean, Cas, and I agreed that 'People Who Are Dead Because of You' and 'Worst Nightmares' should be saved until they could no longer be avoided. It's not going to be fun... not for anyone... not for them, and certainly not for me.
> 
> Sorry if voices got a bit lost tonight... I dunno... I felt like I wasn't batting 1000 this time. I hope it's not too far off though. Feel free to yell at me if it is. It's 5am (and this hasn't been beta'd), and I'm going to bed. G'night, lovies! ♥


	6. Chapter 6

**Notes for the Chapter:**

> Downhill run, people. Not much left now at all!
> 
> **I only plan to do Single Jeopardy and Final Jeopardy... so, no Double Jeopardy round. I just don't have the time or energy to do this all over again with another round. Plus, I didn't plan further than Single Jeopardy. Sorry!**

“And we’re ba—uh, Dean? You still with us? Should I wait while you place an order, or…?”

Dean shook his head, reaffirming his grip on reality and trying not to stare at Cas, now back at his side. “Stuff it. Let’s get this show on the road. People Who Are Dead Because of You for $100.”

“Aww… Let’s be honest now, shall we? They’re not dead because of _me_. They’re dead because of _you_.” Gabriel was answered only by silence and a glare that, had it been a weapon, would have been an Angel Blade. “But, of course, I know what you meant. So, for $100. _She_ died in her mother’s arms, just before her mother committed suicide with Hell Hounds breathing down her neck.”

Silence fell.

There was a pricking at the back of Dean’s throat and a stinging at the corner of his eyes, but no amount of coughing or blinking seemed to quell either.

“Anyone?”

_–buzz–_

“Dean.”

“Yeah. Who was Jo Harvelle?”

“Nice work. I was starting to think you’d forgotten already.”

With fists clenched, Dean made to charge the arrogant trickster of an angel. But, despite Dean never having seen his brother move, Sam stood in his way. “He’s just trying to get at you. He’s not worth it, Dean.”

“She was our _friend_ , Sammy. He can’t talk about her–”

“This is exactly what he wants. Now, go back to your podium and play the damn game. Got it?”

With a shuddering breath, Dean relented. Sam was right, and he knew it. It didn’t make Gabriel any less grating, though. He settled back in and waited for the anger and adrenaline to subside. “I think I’ve had enough of people who are dead. Worst Nightmares for $100.”

“And this brings us to the interactive portion of the program. I’ll press play on my handy dandy angel-remote–” He waved a small black contraption that didn’t look much like any remote Dean had ever seen before. “–then you’ll watch the nightmare and tell me whose head I borrowed it from. Got it? Good. Here we go, for $100.” He pressed play.

_Samuel Campbell is talking on the telephone. He’s telling someone on the other end of the line, “Hey, you do what you like, but don’t say I didn’t warn you. No hunter ever really leaves the life.”_

_As he hangs up, a pair of hands fall to rest on a slightly bulging tummy._

_Scenes flash: Sam and Dean in the Impala, eating greasy fast food. Another of them in a dive motel, Dean lying awake, staring at the ceiling and Sam fast asleep on his laptop’s keyboard. Yet another, unloading guns from the trunk of the car._

_Then comes a barrage of live-action death, rapid fire scenes of lives being taken by stabbing, staking, guns, and more. Deals being made. Dean with demon eyes. Sam drinking demon blood. Each of them dying time and again._

The playback suddenly stopped.

_–buzz–_

“Castiel.”

“Who is Mary Winchester?”

Sam seethed anger. “What?”

Cas dropped his gaze to his hands, where he fidgeted with the buzzer. “It was one of her recurring nightmares. I’ve... been watching over you and your family for a very long time, Sam.”

“That’s correct… if anyone cares.” Gabriel rolled his eyes and crossed his arms impatiently.

“But... NO!”

Dean considered the idea objectively until Sam’s shout pulled him from his thoughts. “No, Sammy, he’s right. Mom’s worst fear was us becoming… well… us.”

“I don’t–”

“Oh, c’mon. We both knew this was the last thing she wanted for us.”

“No, Dean, _we_ didn’t. Because _I_ never even got a chance to know her.”

“Oh, and that’s my fault now?”

“No, of course not, but–”

“Nah, you know what, Sammy? You’re right. You didn’t ever get to know her. But at least you never knew what you were missing.”

“Dean, I–”

Dean ignored him. “Just pick a damn category, Cas.”

“Fine. I… uh…” He huffed a weary sigh. “Worst Nightmares for $200.”

Gabriel pressed a button without uttering a single word, which was more than mildly unsettling. As the scene started to play, it was obvious it wasn’t meant for Dean. And Sam’s face told him everything he needed to know.

_Amelia is standing next to a crib, looking down at an infant. The baby begins to cry, but she freezes as she tries to reach for it. She’s pulled backwards, slamming heavy into a wall. The look on her face is sheer terror as she’s slowly dragged up toward the crown molding and then across the ceiling._

Sam mashed his buzzer repeatedly, probably hoping it would stop the show, but nothing happened.

_Blood seeps from her abdomen, soaking through her sundress. She screams silently, her mouth forming the shape of Sam’s name. As she bursts into flames, a figure is seen standing over the crib, letting blood drip into the baby’s mouth._

 Sam was on the floor, his thumb still depressing the button in his hand. He was trembling, tears streaming down his cheeks, and begging, “Stop. Please. Just stop. It’s mine. What is mine? Please. Just make it stop.” He didn’t sound like he even knew he was talking.

Dean knelt next to him, his hand on Sam’s shoulder. “It’s okay, man. It’s not real. Don’t let him get to you.” His gaze fell to Gabriel, whose smile was a bit too smug for his liking. “He was trying to answer, you dick.” He stood, walking with purpose toward the angel, who no longer looked so smug, and grabbing him by the collar. “You know, we’ve been playing your little game, but I’ve about done with you and all your bullshit. Look at him.” He slung Gabriel toward the spot where Sam was still cowering. “LOOK AT HIM!”

“Oh, no. I’m so scared,” Gabriel mocked.

“Play fair, or–”

“Or what, Dean? What exactly are you gonna do about it?” Gabriel spat his last syllable in Dean’s face. “See, you forget.” He snapped his fingers.

“Huh?” Dean was instantly back behind his own podium, and he took the chance to help Sam to his feet.

Gabriel smoothed the lapels on his suit. “You forget that you’re in _my_ game and _my_ world, where we play by _my rules_. You don’t have to like it, Dean. You just have to stop your whining and play along, or else–”

“Or else wh–”

“Ah, ah, ah. Now, Dean, you don’t really want to ask that, do you? Because you know exactly the sorts of things I can do. Things that are worse than death. So, I suggest you put on your big boy underwear—or your frilly pink satin ones, if you prefer –and play along. What do you say, eh, champ? I’ll even be a good sport and give Sam credit for that one, despite the fact he only sort of phrased it as a question… eventually.”

Dean grimaced but knew there was no other way. They’d never found a way out of one of his games, save for Holy Fire, which they were drastically low on at that given moment. When Sam looked to him for a sign of courage or further resistance, Dean instead shrugged his defeat. “You heard him, Sammy. Pick a category.”

“That’s a good boy.” Gabriel grinned.

Sam appeared to steel himself as he looked over the remaining options. “People Who Are Dead Because of Y–” He paused, shook his head. “Because of Us for $200.”

“ _He_ was more of a father to you than your own father, took a bullet for you, and then went on to become a vengeful spirit after his death.”

_–buzz–_

“Dean.”

“Who is Bobby Singer? Same category, $300.”

“But I haven’t even told you if you’re ri–”

“I’m right,” he growled. “Same category. $300. Read it.”

“Fine. For $300. Her death dragged Sam back into the family business and foreshadowed the deaths of every woman he would ever love thereafter.”

_–buzz–_

“Sam.”

“Who is Jessica… again?”

“Correct. You boys are on a roll. But, first, another commercial break... after the scores. Looks like… Wow! Dean and Cas are currently tied for first with $1300, and Sam’s right behind them with $1200.” The audience oohed ominously. “You better catch up quick, Sam. After all, you’re supposed to be the smart one. And you’ll get your chance to prove it right after this!”

In an instant, Dean was standing in a garden he remembered too well. Sam was with him, dressed in an all-white suit. Sam's perfectly-shined loafer rested on the neck of a struggling man who looked exactly like Dean, and with the twist of his ankle and a sickening crack, the man ceased struggling… and… ya know… living.

“Oh, hello, Dean.” Sam said, eerily calm. “Aren’t you a surprise? You’ve come a long way to see this, haven’t you?”

Dean didn’t need a cue card to tell him his next line; he’d already lived it. “Well, go ahead. Kill me.”

Sam, who was lucky enough to be oblivious to the fact that they were acting out more of a memory than an advertisement, read his part. “Kill you?” He looked toward the not-quite-Dean's corpse that lay in a heap. “Don’t you think that would be a little… redundant?” He paused, sighed. “This must be painful, speaking to me in this… shape.” His expression screamed of confusion as he spoke, but he played the part perfectly. “But it had to be your brother. It had to be.” He reached toward Dean’s shoulder.

Dean pulled away, nearly as disgusted as he had been the first time it happened.

“You don’t have to be afraid of me, Dean.”

“Sammy, stop.” Dean knew the words were wrong, but they were the ones that came out. He cringed as he looked up for his next cue, realizing just how sever the trivialization of his trauma was. “You’re acting like Lucifer.” He held out a candy bar that he didn’t remember having in his hand. “Eat a snickers.”

Sam grabbed it and took a reluctant bite.

“Better?”

“Better.” Sam was back in his normal clothes with a proper Sam expression on his face. He slugged Dean on the shoulder. “Thanks, man.”

A voice over rang out: “You’re not you when you’re hungry.”

**Notes for the Chapter:**

> I take zero credit for this commercial. I got the idea from: http://theangelgabrieldidmyhair.tumblr.com/
> 
> I found it on this post: http://tmblr.co/ZMCbQveqMBMM
> 
> The changes made to it were mine, but the idea was 100% theangelgabrieldidmyhair's.
> 
> Not beta'd... not anything'd... 4am = tired. I hope you enjoyed it, but I'd love feedback either way. 
> 
> It's really almost over! O.O


	7. Chapter 7

**Notes for the Chapter:**

> I'm so sorry it took this long to get you an ending.

“Ah. Memories,” Gabriel cooed, and his smug smile made Dean cringe.

“Memories?” Sam asked. “What’s he talking about, Dean?”

“Nothing. Ignore him. Just pick a category.”

Sam’s concern was visible, but he did as Dean instructed anyway. “People Who Are Dead for $400.”

“She was Sam’s first kiss, but Dean ‘ganked’ her anyway and then lied about it, leaving her son an orphan.”

_–buzz–_

“Sam.”

“Amy,” Sam grunted through clenched teeth, his eyes boring holes into the unflinching profile of Dean’s face. “Finish the category.”

“If you boys aren’t even going to let me—”

The heat of Sam’s glare finally receded from Dean’s cheek as he turned toward Gabriel. “I said, ‘Finish the category.’”

“Touchy, touchy,” Gabriel mocked, but then his expression hitched. “Oh. If you didn’t like that, you’re really going to hate this. For $500. Sam ‘iced’ her at her own request after a haphazard plan to cure her failed.”

Dean’s focus immediately shot to Sam, who surely had the answer. Just because Dean didn’t remember didn’t mean Sam wouldn’t. “C’mon, Sammy. You got this,” he spoke from the corner of his mouth, through a very unnatural grin.

Sam shook his head, the gears turning so fast that Dean thought he might smell smoke. “Dean, I… I-I-I… I can’t remember. I can’t remember her name.”

“Sure you do,” Dean whispered. “The… uh… werewolf, right?”

“I know what she was. I just can’t remember her na—”

“Ah ah ah,” Gabriel tutted. “No cheating. And your time’s almost up. Anybody?”

But no buzzed in. For the first time in twenty-seven questions, no one even dared to hazard a guess. When a buzzer did eventually sound, it only signaled their time running out.

“Really, Sam? I’m disappointed in you.” Gabriel sauntered over, his tone and expression both equally patronizing. “Have there really been so many that you can’t even recall all their names?”

“No, I… dammit.” Sam’s fist landed on the podium with a thud.

“It’s okay, man. It’s only one question. We got this.”

“No, _man_ , it’s _not_ okay. It’s not. I cared about her, Dean. I…” Sam looked warily at Gabriel and lowered his voice to a barely audible whisper. “I slept with her.”

“Well, there ya go!” Gabriel threw his hands up in honor of his new revelation.

“There goes what exactly?”

“Oh, Sam, you must know. It goes with the territory.”

“What are you getting at?”

“Don’t you come with some sort of warning by now? Fornicate at your own risk? Side effects may include death? Something along those lines?”

Sam came away from his podium with a growl, fists clenched as he lunged. But Dean quickly slipped in front of him, stopping him with a hand on each shoulder.

“Sam… Sam…” He snapped his fingers. “Sammy. Like you said, this is what he wants. We got this. Just… just… go back to your buzzer and finish the game, alright?”

“Yeah… yeah… you’re right.” Sam’s eyes narrowed, his fists never unclenching, but he did as he was asked.

Gabriel quietly giggled through the exchange, doing little more than feigning fright at a few choice moments. “You two done? The card says her name was Madison, for what it’s worth.”

“Madison, right,” Dean mumbled under his breath.

Sam only grimaced before scanning the three remaining questions. “Worst Nightmares for $300.”

“For $300.” Gabriel pressed play.

_The scene is set in a motel room, and not a particularly nice one._

 Dean thought it looked vaguely familiar, but it could have been any one of the million he and Sam had stayed in over the course of their lives.

_The wallpaper is yellowed and peeling, and there is an impressive amount of blood spatter on the walls. In the corner of the room, crimson streaks break off from the wall where they instead cover the face of a shocked and frightened Dean Winchester. He looks to be about ten years old, and he’s holding the shredded corpse of six-year-old Sam. Dean still has a shotgun tucked under his arm, but he’s abandoned any attempt to use it. He rocks with Sam’s body clutched to his chest as tears begin to roll down his cheeks._

_Dean’s face begins to pale, and his movement slows. As he loosens his grip on Sam, it is evident that Dean is suffering from a gaping chest wound himself. The blood pool around them grows as Dean visibly struggles to hold on for as long as he can. He whispers an ‘I’m sorry I couldn’t protect’ to Sam and slumps against the wall, also dead._

_–buzz–_

“Dean.”

“Who is… uh…” Dean stopped to blink back what he would swear weren’t tears. “John Winchester?”

“Correct! Give the man a prize! No… wait… scratch that. That’s not how this works at all.”

“D-dad?” Sam sputtered.

“Yeah.” Dean nodded with a raise of his eyebrows, hoping to move on quickly. “Worst Nightma—”

“No. Wait. How would you know that?”

“Read it.”

“You… read it? Where in the hell would you read something like that?”

“Dad’s journal?”

“Boys! Mind saving the family sharing hour for later? I’m not Dr. Phil, and this isn’t—”

“Shut it, Gabriel,” Sam snapped, and Gabriel complied with little more than silent mimicking in response. “Dean, I’ve been through Dad’s journal about a million times compared to your… what? Five? How did you see something like that if I never did?”

Dean barked a nervous laugh and scraped at the podium with his thumb nail. “Hm. Yeah. I _might_ have ripped that page out.”

“Ripped that…” Sam huffed in annoyance. “Ripped that page out? Seriously, Dean? Why? Why would you do something like that?”

“Because.” Dean’s nose wrinkled as winced. He took a deep breath and tried to keep the anger out of his voice, though his efforts went mostly to waste. “Because I didn’t want you to read that. I didn’t need you to think about something that… that… awful. It was graphic and violent and… just… fucked up, Sammy. I didn’t need you to ever think about that or picture it. I sure as _hell_ didn’t ever want you to see it.” He paused to glare at Gabriel with nuclear-meltdown levels of contempt before turning his attention back to Sam. “All I ever wanted was for you to feel like you grew up in a sort of normal way… at least, as normal as life ever was for us. On top of everything else, you didn’t need to know that, when Dad did make it ‘home’ to sleep, he tossed and turned to images of us being slaughtered. Okay? You happy now?”

The confusion and anger in Sam’s eyes softened to a gentler, more familiar pain. “Yeah. Elated.”

“Good. Worst Nightmares for $400.”

Gabriel didn’t respond at first. But, when Dean snapped his fingers several times in succession, he jumped. “Oh! Me? Am I allowed to speak again? Thank you so much, kind sir,” he said mockingly.

“Oh, just press the damn thing, will you?”  Dean waved his hand absently in the direction of the button.

“As you wish!”

_A park bench sits amidst a thin fog. Off to the right is a tall fence with an ornately designed gate, and the finish is an almost pearlescent white. A darkened figure is seen, lit heavily from behind, as it approaches the bench. Once seated, it is clearly Castiel. He crosses his legs at the ankle and glances at his wrist as if checking a watch for the time. He looks around anxiously before staring off into the middle distance for a few long seconds and then looks at his wrist again._

Dean could see Cas squirming slightly in his peripheral vision, the angel’s thumb repeatedly mashing the buzzer. His left eye started to twitch slightly, and he began gritting his teeth loudly enough that it caused Dean to shudder.

“Stop. Please, just stop. It’s mine,” Cas whispered to no one in particular. He shook his head slowly with a deeply unsettling sadness in his eyes. “Don’t make him watch the rest.”

Dean’s hand settled on Cas’ shoulder. “Hey, man. It’s okay. It’s not real.”

“No, Dean. It’s not okay.” The metallic ting of Cas’ Angel Blade rang out as it appeared in his hand. “Stop it, Gabriel. STOP IT!”

“Ah ah ah!” Gabriel simply lifted his hand in Cas’ direction and pinned him in place with a flick of the wrist. “Wait your turn, Brother.” He spat the familial title derisively, as if it were some vile intrusion that had taken up residence on his tongue.

Dean’s brows knitted together in confusion as he turned back toward the scene still playing out.

_Castiel rises to his feet and paces. He checks the time again and stumbles to the gate, grabbing hold of the bars to stabilize himself when his knees go weak. “They’re not coming, are they?” he asks into the darkness._

_With the flutter of wings, he disappears and the scene briefly goes black. When the lighting level rises, Castiel is seen standing in a cemetery. He searches headstones frantically and stumbles again as he slows his steps. He clumsily moves the last few yards and drops to his knees before two nearly identical stones. They’re simple and undoubtedly inexpensive._

Dean knew what they would say before he even saw them, but he still squinted to read the etching.  

_Dean’s and Sam’s names are carved into the stone. Their birthdates read correctly, and their dates of death are the same._

The date isn’t nearly far enough away for Dean’s liking, and Sam’s expression suggests that he concurs.

Castiel crawls to Dean’s headstone and slumps against it. His hands are in his hair, his elbows resting on his knees. Tears trail down his cheeks as he utters an unending string of ‘no no no no no no,’ and the scene fades.

Cas’ buzzer finally sounded, but it was somehow more hollow than it had been previously.

_–buzz–_

“Castiel.”

“Who am I? Who is me? What is mine? I don’t know how to answer this in the form of a question.”

“Correct!”

“Yeah, yeah, yeah.” Dean waved away Gabriel’s response. “Would someone mind telling me what the _hell_ I just watched?”

“Aww. Would you like to tell him, Castiel? Or shall I?”

“No.” The hardness slipped from Cas’ expression as he turned to Dean. “It’s my dream, my _nightmare_ , and I should be the one to explain it to you.”

“Wait. How do you dream if you don’t sleep?”

“It’s… more of a vision. A recurring vision I’ve had since the first moment I met you.” Cas leaned forward to look at Sam. “Both of you.”

“And you’re scared we’re gonna die? Because, I hate to break this to you, but we all gotta go sooner or later. I mean, I was hoping for later—” Dean chuckled. “—but let’s be honest, sooner’s just more likely in our line of work.”

“No, Dean. It’s not about you dying, or even about you dying… prematurely. It’s…”

“It’s what?”

“It’s…”

“It’s what happens after you die,” Gabriel chimed in. “You see, poor little Castiel is afraid that, for all the good you’ve done and all the lives you’ve saved, it still won’t be enough to cancel out the evil. All that time you two spent in Hell, all the torturing and chugging demon blood like it was going out of style, it twists and warps souls into something unrecognizable. And he isn’t sure that either of you will ever be admitted into Heaven.”

“Is… is that true, Cas?” Dean felt a pang of grief and betrayal swelling in his chest.

Cas nodded. “It’s… all true.”

 “Wait a minute. You mean to tell me that after all we’ve done, we might still not be good enough for Heaven?” Sam asked incredulously.

“I… don’t know. I’m sorry, Sam. I wish I did, but I don’t.”

“Heh. Screw Heaven,” Dean said, trying to shake off the filth of his own emotions. “Who needs ‘em anyway, right, Sammy?”

“Yeah. Right.” Sam smiled a smile that looked forced.

“Dean, you don’t understa—”

“Come on, Cas. One question left.” Dean nodded at the board. “Let’s just get this over with, ‘kay?”

“Of course.” Cas’ gaze dropped to the fake wood-grain of his podium. “Last question, please.”

Dean braced himself for whatever he was about to see. If the pattern held, his nightmare would be the last, and he didn’t even know what it would be. It had been years since he’d remembered a dream that wasn’t some memory of Hell or Purgatory playing out behind his eyelids.

_Footsteps echo against the cement floor of a mostly empty warehouse. Dean’s voice is heard calling out to Sam and Castiel, but neither answers. He calls out again, and Sam responds._

A wave of nausea swept over Dean at the sound of it. He wasn’t sure why, but it struck a chord in his memory, setting off some natural reaction to a scenario he couldn’t quite remember. His knuckles went white where he gripped the lectern, and he fought back the urge to vomit with every ounce of will in his body.

_The sound of Dean’s footsteps stops, but a new set picks up from the other direction. Dean hurries toward the sound, searching the darkness for Sam and Castiel. As he reaches the far end of the building, the tall, foreboding silhouette of Sam begins to take shape. He’s pacing._

But Sam’s gait was all wrong. His steps were lighter and more graceful than normal. Dean’s stomach churned again, the contents of his stomach clawing their way up his throat.

_“Hello, Dean,” Sam says. “Long time no see.”_

Dean retched, coughing and choking as the first taste of bile filled his mouth. The voice was Sam’s, but the tone and cadence were very much not.

_“Lucifer,” Dean replies, his voice little more than breath. “What the fuck do you think you’re doing in my little brother?”_

_“You mean my vessel?”_

_“I mean my little brother.”_

_“Just taking him for a ride.” Sam’s eyes widen suggestively. “I always did love being inside him. He fits me so well—so warm and tight. And he fights just enough to keep things interesting, but never enough to stand a chance at winning.”_

As Dean doubled over, dry heaving turned to vomiting. There was a sickening warmth in the pit of his stomach, and the purging hadn’t relieved it a single iota. Both Sam and Cas rushed to his side, but he pushed them away as it played on.

_The harsh industrial lighting glints off of something in Sam’s hand, and it draws Dean’s eye. “What… uh… what’ve you got there?”_

_“Oh, this?” Sam holds out an Angel Blade, blood soiling the length of it and dripping from the tip. “Just a bit of sibling rivalry.” Sam scoffs and jerks his head roughly toward the wall._

_Dean pushes past him, the light following. A wall of primitive, unmaintained cinder blocks climb upward, a figure slumped against them. Castiel looks to be in pristine condition, save bloodstain on the front of his shirt, ever expanding from beneath his tie, and his oft unseen wings now charred forever on the wall and floor. His eyes are open, and he is still. His lips are still pink and barely parted, but the blood has started to drain from his face._

_Dean drops to the ground and shakes the angel’s limp and empty vessel. “No. No, no, no. Why?” He turns sharply toward Sam. “Why would you do that?”_

_“He was becoming just as flawed as the rest of your hairless apes, becoming so human. He had decided to fall for you, Dean. I had to do something. It was disgusting. Consider it a mercy killing.”_

_“He… he what?”_

The floor of the studio was unrelenting as Dean’s knees crashed into it, and his hands stung where he caught himself before toppling face-first. His chest and throat burned as he vomited again. The force of his retching was indescribable, the sensation punctuated by blood vessels bursting across around his eyes and across his neck and shoulders.

“Why are you doing this?” he gasped between heaves. The next one was dry again, his stomach as empty as his heart and soul felt. And he found himself wishing for a sucking chest wound to account for the pain that couldn’t possibly be attributed to emotional trauma.

Gabriel just laughed, and Cas insistently took his place Dean’s side. He knelt next to Dean, rubbing soothing circles on Dean’s back.

_“He was prepared to choose your kind—to choose you—over his family. So, I ended him before he did something he would come to regret later.”_

_Dean lifts Castiel’s hand to his mouth and presses kisses against his knuckles. Inside Castiel’s still-clenched fist, Dean finds the amulet Castiel had once returned to him that he’d prompt discarded in the nearest trash can. He gathers the lifeless form in his arms and holds it close to his body. Gentle sobbing is heard, though Dean’s face is buried in the lapel of Castiel’s trench coat._

_Sam moves to stand behind Dean and squats to place his hand on Dean’s shoulder. “It never would have worked. I did you fav—”_

_Dean spins in place and slides Castiel’s Angel Blade into Sam’s chest without hesitation, causing Sam to fall forward. He coughs blood onto Dean’s shirt, his hip dropping to the floor. As the reality of the situation crashes down around Dean, he sits back against his heels and pulls Sam’s back flush against his own chest._

_“I’m sorry, Sammy. I’m so sorry,” he whispers as tears burn red streaks down his face._

_“It’s not your fault, Dean.” Sam finds the strength to overpower the angel dying inside of him enough to speak, though his voice is distorted by the blood in his throat and lungs. “You did the right thing. Thank you.” The final syllable is exhaled in his last breath._

_In one final act of cruelty, Lucifer’s wings burst outward from his body, forever burning themselves into Dean’s flesh._

By the end of the scene, Dean’s face was a mess of snot, saliva, and tears. He was gasping for air, which refused to come. His limbs threatened to buckle beneath him, and he was shaking uncontrollably. Still, he blindly fumbled with a shaky hand trying to find the buzzer he’d long since abandoned.

When he found it, he clambered, trembling, to his feet, Cas supporting the majority of his weight. He depressed the button until it buzzed. “Who is me?” he answered and then slammed the plastic device into the podium’s surface until it shattered into a million piece. “Now, why? Why are you doing this?”

Gabriel sauntered casually across the studio floor and swept his hand through Dean’s hair. “Don’t you see, Dean? You got cocky. You started to that things were finally looking up. You dared to become optimistic. And it was my job to show you the truth.”

“The truth?”

“That it always ends the same. No matter how hard you try, you’ll never win. And you always wind up surrounded by the people you love most, all dead because of you.”

“Wh-what am I supposed to do?”

“Give up! Angel Tablet. Demon Tablet. All of it. Just give up, and maybe… just maybe… you won’t lose everybody you love.” Gabriel looked thoughtful and then grinned. “I mean, you probably will anyway. But it’s worth a try, right?”

Dean grabbed Gabriel by the shirt front and growled, “The next time I kill you, it’s going to be for good.”

“Ooh! I’ll look forward to it.” Gabriel bit his bottom lip in anticipation. “Catch me if you can!” And, with a snap of his fingers, he was gone—as was the studio, the lights, and the live audience.

Instead, they found themselves sitting back in The Yankee Clipper, still in Ankeny, Iowa.

“Uh, Dean… we gotta go,” Sam said, his voice trembling.

The scene all around them was gruesome, the bar absolutely littered with corpses—staff and patrons alike. And without a second thought, they made a run for the Impala. That night, the news on every channel talked about the Ankeny Massacre and showed people gathering in memoriam of all who died. Families mourned their lost loved ones, and children cried out for parents who would never return home

 All too used to leaving tragedy in their wake, Dean flipped off the TV. Those strangers had died senselessly, but his brother and angel lived another day. It was the most he could ask for after the day they’d just had.

After dinner, Sam quickly drifted off to sleep. When Dean retired to his bed, Cas stood hesitantly beside it. “May I… sit with you?”

Dean gave a jerky nod in the affirmative and scooted over to make room.

Cas slipped off his shoes, coat, and jacket before sinking on to the bed next to Dean. After a long silence, he finally spoke. “I would, you know.”

“Would?” Dean’s eyebrows retreated toward his hairline.

“Fall… for you. _Have_ fallen for you already, in a manner of speaking.”

“Yeah… uh…” Dean cleared his throat. “Likewise, I guess.”

Cas slunk down the headboard and offered Dean his shoulder. After a short deliberation, Dean accepted, curling into Cas’ side and timidly laying his arm across the angel’s chest.

“Are we gonna be okay, Cas?” Dean threw a glance toward Sam. “All of us?”

“Would you like me to lie to you in order to make you feel better?”

Dean chuckled. “Yeah, I think I might, just for tonight.”

“Yes,” Cas replied and placed his hand atop Dean’s. “I believe we will.”

“Heh. Will you tell me the same thing if I ask again tomorrow?”

“Yes.”

“Are you still lying?”

“I guess you’ll just have to wait and ask me again tomorrow.”

Dean smiled his thanks and drifted off to his first fitful night of sleep in years. He awoke without a single memory of his dreams, for which he was always thankful. And he never saw fit to ask that question again.

As he had learned over the years, some questions were better left unanswered. And, for a while, living to fight another day alongside the people he loved could be enough. In fact, he had inkling that, for the rest of his life, it would definitely be enough. And, had he been blessed with psychic abilities, he could have told you that it absolutely was.

**Notes for the Chapter:**

> Okay. Over. Done. Not beta'd or checked over in any way. I've been up for god knows how long. I don't even know if the sentences were cohere toward the end. I'm sorry the end isn't better. Maybe I'll try and fix it someday... maybe. Or not. I'm really just happy to be done with this. I hope it's not too much of a disappointment.
> 
> Since it's nearly 10am, I should probably sleep. Sorry again... for stuff and things. Leave me comments if you want. I like comments. God, I'm tired.


	8. Epilogue

**Notes for the Chapter:**

> I sort of hated the ending. It didn't *feel* like an ending to me. So, I decided to write this epilogue. It's a look far into their future... in stages. This is how I dream of the series ending, though it never, ever would. I just... I thought I'd share it with you.

Gabriel's final words haunted the boys for years. Dean, especially, spent a good long time waiting for the other shoe to drop... even more than usual. But plans kept progressing, and they managed to stay alive through it all. At some point, they agreed that maybe it was just a scare tactic to make them stop. They were too close to winning, and nothing slows people down like fear. Moral of the story: Never underestimate Team Free Will. They never heard from Gabriel again.

Eventually, Sam slammed the doors on Hell, locking those black-eyed bitches away where they belonged. And Cas inevitably fell, closing the doors of Heaven behind him. Once the world was a safer place, Dean and Cas finally even hazarded a chance at a life together.

***

Dean stood at an altar, his tux nearly choking him, with Cas at his side. His palms were sweaty, but Cas entertwined their fingers anyway. To Dean's other side was Sam, who wore a tight smile and was obviously trying to look calmer than he felt. When the bridal march began to play, Dean clapped Sam on the shoulder.

"You read for this, man?"

"I don't know," Sam admitted through a fake grin.

"Attaboy!"

The doors opened, and a radiant brunette (named Elle) entered in a long white dress. Her smile was as genuine as Sam's was not, but he instantly lit up at the sight of her. Dean remembered the expression fondly, though he'd only ever seen a few times when they were young and had managed a decent Christmas.

She made her way to the altar, and she and Sam repeated as they were told. Rings were exchanged, and they shared their first kiss as husband and wife. Cas barely even smirked when Dean wiped away a tear.

***

A few years passed. Dean and Cas were in their tuxes, but they stood in front of a cake. They both gripped the handle of a knife and were cutting a chunk to share. It was no surprise when Cas got distracted and ended up with frosting on his cheek, just as it was no surprise when Dean kissed it away.  It was Cas' refusal to feed Dean in return that caught everyone off guard. A silence fell, but all was soon explained when one of catering staff wheeled out a cart with a covered platter in the center. Sam's smile was almost as wide as Dean's when the lid was lifted to reveal Cas' big surprise—Dean's favorite pie. If ever he'd doubted it before, Dean finally knew for certain that he'd made the best decision of his life.

Everyone danced and celebrated, but Sam and Elle ducked out early. At seven-and-a-half months pregnant, she could only take so much partying, and she was being absolutely plagued with heartburn. Sam and Dean agreed that if heartburn was the worst of their problems, things had certainly changed for the better.

***

Sam's son, Bobby, was six months old. Elle tucked him into his crib as Sam leaned against the doorway. He watched pensively. He couldn't shake the feeling that something bad was about to happen at any given moment. He knew how that story ended; he had watched it play out in his own infancy. When Elle took his hand and led him to bed, he felt the dread in the pit of his stomach lessen. She knew him better than he knew himself, though. Nothing could get past her, and it never had. She offered him a few words of reassurance and a tender kiss goodnight. They drifted off to sleep and awoke safely the next morning (and many other mornings still to follow). She didn't even say, "I told you so."

***

Everyone sat gathered around a dinner table. Dean and Cas; Sam, Elle, and Bobby (now age 7); Garth, who refused to settle down; and the Tran's, now cosisting of Kevin, Amanda (his wife), their daughter, and Linda (who wouldn't put her granddaughter, Erica, down for love or money). If the tree and gifts were any indication, it was Christmas. After dinner, everyone sat around sipping wine, beer, or eggnog and watching the kids rip into brightly colored paper. By the time everyone left, the floor was a graveyard of shredded wrapping paper and discarded bows. Cas called it the most beautiful disaster area he had ever seen.

***

Dean and Cas smiled nervously at each other. They couldn't believe their luck. As they reached to join hands, their union was happily interrupted with the tiny hands of their new daughter. She was four years old and perfect in every way. Dean insisted they call her Jo.

"Can we go home?" she asked. "I'm bored."

Dean squatted next to her. "Would you like that? To go home?"

"Yes, please."

"Because I was thinking—" He paused to grin at Cas. "—that we might stop for ice cream first. But if you want to go home inst—"

He was interrupted when Jo flung her arms around his neck. "Can we really, Daddy?'

"Of course, baby. Anything for my princess."

He stood and took her hand again as he and Cas led her to their car, a roomier, more family friendly vehicle than Dean was once accumstomed. It had been a long ordeal, but she was finally, _legally_ theirs. How else do you celebrate if not with ice cream?

***

Sam was barely 42 the day he held a set of keys toward his eldest child. Bobby grinned, obviously surprised by the gesture. He cautiously reached for the keys but stopped to stare disbelievingly once again at the Impala to which they belonged.

"You sure?" he asked.

“Go ahead," Dean encouraged him from behind Sam. "She's all yours. But be good to her, you got that?”

The moment was punctuated by the laughter of Sam's younger son, Mark, who was drastically losing a game of H.O.R.S.E. to Jo. After Bobby pulled away, Dean and Sam joined their other kids to play as teams. At dusk, Elle and Cas called them in for dinner. It was a good night.

***

Some twenty years later, Sam found himself standing in a graveyard, surrounded by his friends and family. Elle’s name was on the headstone. She was tragically young, but she died of natural causes. Even though tears streaked Sam's cheeks, he smiled.

"Why the smile?" Dean asked. "Not that I'm complaining."

Sam explaind that he was sad to see her go, but he was so thankful for their time together. He glanced at his sons and admitted that he considered them miracles. He never thought he would get the life he had with Elle, because he always believed his love was a death sentence.

"Nonsense, Sammy. I _always_ knew you'd have this life." Dean hugged him tight and then left him to mourn privately with his children. He never remarried.

***

After Cas fell, he began aging like any other human, and Dean found it fascinating to watch his angel change. Sitting around a picnic table—complete with a checkered tablecloth—in Sam's backyard, Dean (now well past retirement age) sipped his beer and studied the fine lines around Cas' eyes and mouth. He lookeed lost in thought.

"What's up, Dean?" Sam asked.

“It was all worth it, wasn’t it?” Dean replied, now staring off into the middle distance.

The sound of their grandchildren playing served as background music, and Cas reached out to squeeze Dean's hand.

Sam glanced at their clasped hands and then out at the squealing children, who were pretending to fight monsters in a world where monsters no longer existed (thanks to them). “Yeah... It was all worth it,” he said.

"You ever regret coming with me that night I showed up and told you Dad hadn't been home in a few days?"

"Plenty of times." Sam chuckled. "But not anymore."

"You sure?"

"And miss out on all of this? Are you kidding me? Why? Do you regret coming to find me?"

"Every damn day of my life." Dean grinned and winked when Sam tried his best to look offended.

"Jerk."

"Bitch."

"Hey! Assbutts! Do you mind lowering your voices? They can hear us, you know. Jo'll have our heads if we send her kids back talking like that."

In the distance, the kids sang a faint chorus of 'assbutt, assbutt, Papa said assbutt,' and Cas winced against his hand.

The Impala had eventually made her way back to Dean and had a good view of the backyard from where she was parked in the driveway. Dean still spared her more than her fair share of glances, as she would always be his first love. The sun glinted off her chrome and caught his eye, even if only briefly. He knew it was impossible and daren't admit it aloud, but he could have sworn she looked happy. And, had she been blessed with a mouth, she would most certainly have confirmed it. After all, her boys had turned out alright, and when you run with the Winchesters, that's about all you can ask for.

**Notes for the Chapter:**

> I don't know if this is better or worse than ending at chapter 7. Sorry if it's worse. I don't even know what I'm doing anymore.


End file.
